Tris[3,5-bis(trifluoromethyl)phenyl]borane

Base Information

• Chemical Name: Tris[3,5-bis(trifluoromethyl)phenyl]borane
• CAS No.: 169116-84-1
• Molecular Formula: C24H9BF18
• Molecular Weight: 650.118
• DSSTox Substance ID: DTXSID40572751
• Nikkaji Number: J1.083.491K
• Wikidata: Q82461228
• Mol file: 169116-84-1.mol

Synonyms:tris[3,5-bis(trifluoromethyl)phenyl]borane;169116-84-1;SCHEMBL135550;DTXSID40572751;BPKXQSLAVGBZEM-UHFFFAOYSA-N

Chemical Property of Tris[3,5-bis(trifluoromethyl)phenyl]borane

Chemical Property:

• PSA: 0.00000
• LogP: 8.31560
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 3
• Exact Mass: 650.0509874
• Heavy Atom Count: 43
• Complexity: 741

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(C2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F

Technology Process of Tris[3,5-bis(trifluoromethyl)phenyl]borane

There total 6 articles about Tris[3,5-bis(trifluoromethyl)phenyl]borane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) → tris[3,5-bis(trifluoromethyl)phenyl]-borane (169116-84-1)

Guidance literature:

3,6-bis(trifluoromethyl)bromobenzene; With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -20 - 0 ℃; for 0.5h; Inert atmosphere;

With boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; at -50 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c2dt30384a

Reference yield: 65.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) + boron trifluoride diethyl etherate (109-63-7) → tris[3,5-bis(trifluoromethyl)phenyl]-borane (169116-84-1)

Guidance literature:

With CH(CH₃)2MgCl; In tetrahydrofuran; 1. CH(CH3)2MgCl, C6H3Br(CF3)2, THF (-20°C to 0°C), 1/3 BF3*O(C2H5)2 (-50°C to room temp.); high vac. sublimation (80°C, 1E-6 mbar); elem. anal.;

DOI:10.1039/c2dt30384a

Reference yield:

C28H17BF18O (1421229-24-4) → tris[3,5-bis(trifluoromethyl)phenyl]-borane (169116-84-1)

Guidance literature:

at 80 - 150 ℃; for 72h;

upstream raw materials:

[(C₂H₅)3P]2Pt(CH₃)[(C₂H₅)2O]⁽¹⁺⁾*B[C₆H₃(CF₃)2]4^(1-)=[(C₂H₅)3P]2Pt(CH₃)[(C₂H₅)2O]B[C₆H₃(CF₃)2]4

[(Me₃PtOTf)4]

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate

3,6-bis(trifluoromethyl)bromobenzene

Downstream raw materials:

C₃₅H₂₉BF₁₈N₂

B{3,5-bis(trifluoromethyl)benzene}₃(Et₃PO)

Refernces

BAr^F₃-Catalyzed Imine Hydroboration with Pinacolborane Not Requiring the Assistance of an Additional Lewis Base

10.1021/acs.organomet.7b00381

The research explores the use of tris[3,5-bis(trifluoromethyl)phenyl]borane (BArF3) as a highly effective catalyst for the metal-free hydroboration of imines, a process that is crucial for the preparation of amines. The study demonstrates that BArF3 outperforms other Lewis acidic boranes, such as the commonly used tris(pentafluorophenyl)borane (B(C6F5)3), in facilitating the reaction of ketimines and aldimines with pinacolborane (HBpin) at room temperature without the need for an additional Lewis base. The researchers concluded that the steric hindrance caused by the six ortho fluorine atoms in B(C6F5)3 accounts for its lower reactivity compared to BArF3. The study provides a new protocol for imine hydroboration that does not require external Lewis bases and offers insights into the mechanism of the reaction, suggesting that BArF3 coordinates with the imine nitrogen atom, activating it for hydride transfer from HBpin. The work highlights the importance of steric effects in catalysis and contributes to the understanding of boron Lewis acid catalysis in organic synthesis.